Versatile synthesis of fused tricyclic 1,2,4-triazole derivatives

Synthetic Communications

Volumn 41, Issue 7, 2011, Pages 963-975

  Ellis, David ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

1,2,4 triazole; Fused tricyclic ring system; Intramolecular reduction cyclization; Suzuki reaction; Vicarious nucleophilic substitution

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; OXADIAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; ONE POT SYNTHESIS; SYNTHESIS;

EID: 79952568976     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003707170     Document Type: Article

References (22)

1. Brown, A. D.; Calabrese, A. A.; Ellis, D.; Watson, L. Substituted triazole derivatives. WO Patent 2005121152, 2005.
2. For some representative examples of this transformation, see (a) Brown, A. D.; Calabrese, A. A.; Ellis, D.; Sciammetta, N. Preparation of triazole derivatives as oxytocin antagonists for treatment of sexual dysfunction. WO Patent 2007017752, 2007;
3. (b) Kakefuda, A.; Suzuki, T.; Tobe, T.; Tahara, A.; Sakamoto, S.; Tsukamoto, S. Discovery of 4,5-diphenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human V1A receptor. Bioorg. Med. Chem. 2002, 1905;
4. (c) Garcia, M. A.; Martin-Santamaria, S.; Cacho, M.; Moreno de la Llave, F.; Julian, M.; Martinez, A.; De Pascual-Teresa, B.; Ramos, A. Synthesis, biological evaluation, and three-dimensional quantitative structure-activity relationship study of small-molecule positive modulators of adrenomedullin. J. Med. Chem. 2005, 4068;
5. (d) Carlsen, P. H.; Jorgensen, K. B. Synthesis of unsymmetrically substituted 4H-1,2,4-triazoles. J. Heterocycl. Chem. 1994, 805;
6. (e) Balsells, J.; DiMichele, L.; Liu, J.; Kubryk, M.; Hansen, K.; Armstrong, J. D. Synthesis of [1,2,4]triazolo[4,3-a]piperazines via highly reactive chloromethyloxadiazoles. Org. Lett. 2005, 1039.
7. Makosza, M.; Owczarczyk, Z. Reactions of organic anions, 161: Dihalomethylation of nitroarenes via vicarious nucleophilic substitution of hydrogen with trihalomethyl carbanions. J. Org. Chem. 1989, 5094.
8. Makosza, M.; Golinski, J.; Baran, J. Vicarious nucleophilic substitution of hydrogen. Acc. Chem. Res. 1987, 282, and references cited therein.
9. Ellis, D. Alternative approach to 1,2,4-triazole-3-carboxamides. Synth. Commun. 2009, 2585.
10. For some representative examples of this reaction, see (a) Borg, S.; Estenne-Bouhtou, G.; Luthman, K.; Csoeregh, I.; Hesselink, W.; Hacksell, U. Synthesis of 1,2,4-oxadiazole-, 1,3,4-oxadiazole-, and 1,2,4-triazole-derived dipeptidomimetics. J. Org. Chem. 1995, 3112;
11. (b) Lundin, N. J.; Blackman, A. G.; Gordon, K. C.; Officer, D. L. Synthesis and characterization of a multicomponent rhenium(I) complex for application as an OLED dopant: Signal-amplifying conjugated polymer-DNA hybrid chips. Angew. Chem., Int. Ed. 2006, 2582;
12. (c) Lee, K.; Rouillard, J.-M.; Pham, T.; Gulari, E.; Kim, J. Signal-amplifying conjugated polymer-DNA hybrid chips. Angew. Chem., Int. Ed. 2007, 4667;
13. (d) Roenn, R.; Gossas, T.; Sabnis, Y. A.; Daoud, H.; Aakerblom, E.; Danielson, U. H.; Sandstroem, A. Evaluation of a diverse set of potential P1 carboxylic acid bioisosteres in hepatitis C virus NS3 protease inhibitors. Bioorg. Med. Chem. Lett. 2007, 4057;
14. (e) Garfunkle, J.; Ezzili, C.; Rayl, T. J.; Hochstatter, D. G.; Hwang, I.; Boger, D. L. Optimization of the central heterocycle of α- ketoheterocycle inhibitors of fatty acid amide hydrolase. J. Med. Chem. 2008, 4392;
15. (f) Koufaki, M.; Kiziridi, C.; Nikoloudaki, F.; Alexis, M. N. Design and synthesis of 1,2-dithiolane derivatives and evaluation of their neuroprotective activity. Bioorg. Med. Chem. Lett. 2007, 4223;
16. (g) Goertz, V.; Goodby, J. W. Enantioselective segregation in achiral nematic liquid crystals. Chem. Commun. 2005, 3262.
17. For reviews of the Suzuki-Miyaura coupling, see (a) Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 2457;
18. (b) Littke, A. F.; Dai, C.; Fu, G. C. Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions. J. Am. Chem. Soc. 2000, 4020.
19. For reviews on catalytic transfer hydrogenation, see (a) Ranu, B. C.; Sarkar, A.; Guchhait, S. K.; Ghosh, K. Catalytic hydrogen transfer reductions using ammonium formate: A review. J. Indian. Chem. Soc. 1998, 690;
20. (b) Rajagopal, S.; Anwer, M. K.; Spatola, A. F. Catalytic transfer hydrogenation and hydrogenolysis by formic acid and its salts. Peptides 1994, 11;
21. (c) Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D. Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds. Chem. Rev. 1985, 129.
22. Yang, B. V.; O'Rourke, D.; Li, J. Mild and selective debenzylation of tertiary amines using α-chloroethyl chloroformate. Synlett 1993, 195.